Cassie Continues BOMBSHELL Testimony, Diddy’s Defense Preps

Day three has commenced, and TSR is back on the ground at the federal trial of Sean “Diddy” Combs, taking place at the Daniel Patrick Moynihan U.S. Courthouse in New York City. As The Shade Room previously reported, Casandra “Cassie” Ventura initially took the stand on Tuesday, May 13, to begin her testimony against her former boyfriend. On the stand, the singer recounted alleged “frequent” abuse at the hands of the Bad Boy head. In addition, alleged drug-fueled “freak-offs,” and allegedly being urinated on by male escorts. On Wednesday, May 14, Cassie’s testimony is expected to continue. Furthermore, the 55-year-old’s defense team is also expected to begin their cross-examination.
What to expect from Cassie’s testimony on Wednesday: Prosecutor Emily Johnson says she’ll question Cassie about her 10-year relationship with Diddy for about half the day today before defense lawyers begin their cross-examination.
Here’s a recap of EVERYTHING she said on the… pic.twitter.com/i00bhO5tyY
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Jadriena Solomon
TSR’s Trial Watch Live Updates: Court Arrivals As Cassie’s Continued Testimony & Cross-Examination Is Awaited
TSR was able to catch up with Cassie’s lawyer, Douglas Wigdor, who spoke about his client sharing her “truth” and their journey to the “finish line” of justice. Additionally, Brian Steel, an attorney for Diddy, also shared a few words.
Furthermore, on day 3, Diddy’s family was seen arriving at the courthouse once again. To note, Diddy’s twin daughters, Jessie and D’Lila, were not seen.
#TSRTrialWatch Day 3: Diddy’s mom and sons Quincy, Christian, and Justin arrive at the Southern District of New York courthouse.
Twins & Chance did not arrive alongside them. pic.twitter.com/SdOE8jQ76I
— TheShadeRoom (@TheShadeRoom) May 14, 2025
Cassie’s Testimony Resumes: Drives, Alleged Violence, An Impacted Friendship & More
Cassie took the stand and was presented with two apparent [hard] drives. A.U.S.A. Emily Johnson referred to the drives as “GX 8.” In turn, Cassie told the court the drives contained “messages and photos” from her device.
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As her testimony continued, the footage of the altercation between Diddy and Cassie at the Los Angeles hotel in 2016 was shown again. Furthermore, Cassie noted that as the clip rolled, Diddy could be seen holding her cell phone in his hand. Additionally, another point of the clip shows Diddy throwing glass vases at the singer.
“I just remember it coming towards me. I remember it hitting a wall,” Cassie explained.
After the incident, Cassie says that she saw a close friend of hers, model Kerry Morgan. Morgan reportedly called the cops to report the incident.
“She was upset when she called me. She called the police,” Cassie said.
Ultimately, Cassie explained that the police responded to the incident. However, she “wasn’t ready,” seemingly, to step away from the relationship.
“Just in that moment, I didn’t want to hurt him that way,” Cassie said, per New York Post. “Just too much going on. It was a lot for me in that moment, and I wasn’t ready.”
Cassie was shown a photo in court, “What are you wearing?” Attorney Johnson asked.
“A gown and sunglasses. I had a black eye.” she replied.
She added she had bruises on her leg but changed clothes before the pic — taken with Diddy at an afterparty.
— TheShadeRoom (@TheShadeRoom) May 14, 2025
According to the New York Post, Cassie added that Diddy texted her after the assault.
“You’re going to abandon me all alone. Call me now,” he reportedly wrote. “I got six kids. Pls call me. I’m getting arrested.”
In turn, Cassie reportedly texted Diddy to “[stay] far away from [her.]”
By: Jadriena Solomon
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On The Stand: Cassie Identifies Apparent Male Escorts Used In “Freak-Offs,” & Details Experiences
As her testimony continued, Cassie was shown photos of various male escorts. In turn, she shared how she and Diddy allegedly identified the men.
Attorney Johnson shows Cassie various photos of male escorts asking, “Who’s this?”
Cassie: “Islander. He was on Latin Men. We used him in LA and maybe Vegas.”
“Who’s this, 2A-616?”
Cassie: “We called him Tommy.”“Who is this?”
Cassie: “Greg, an escort in Miami.”“Who’s this?”…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
Additionally, Cassie explained that she tried to avoid kissing the escorts amid the freak-offs.
“I tried to avoid kissing — it seemed too intimate. But Sean told me to do it, to kiss the escorts,” she said.
Per the New York Post, Cassie reportedly celebrated her 29th birthday at the Blind Dragon club in West Hollywood. However, during the night, she says, Diddy “pulled [her] out” of the celebration “so many times that [she] just gave up.”
Cassie testified Diddy made her do a “freak off” on her 29th birthday — “He had me pulled out of Blind Dragon for the freak-off.”
Blue Dragon was a karaoke lounge in West Hollywood.
She said he used the freak-off videos to threaten her:
“He wanted me to fear… to hurt me……— TheShadeRoom (@TheShadeRoom) May 14, 2025
Per the singer, Diddy made Cassie “fear” for her career.
“I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” she said.
By: Jadriena Solomon
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On The Stand: Cassie Details On & Off Drug Addiction Sparked From “Freak-Offs”
Per the New York Post, Cassie continued her testimony, explaining that she developed an “on-again-off-again” opioid addiction sparked by the consistent freak-offs.
“[They] made me feel numb, which is why I relied on them so heavily,” she explained.
Furthermore, she explained her use of the substance after the encounters.
“I’d take opiates… I wanted to feel numb. We’d get massages, I.V. fluids. The chef would cook us something,” she said. “[I used them] often. I got Urinary Tract Infections.”
AUS Attorney Johnson asked Cassie to detail her Urinary Tract Infections, “Were the U.T.I.s painful?”
“Very. Anti-bacterial didn’t work anymore.” She replied.
Johnson: “How did it feel, during freak-offs?”
“Burning. I would not advise it.” Cassie replied.
— TheShadeRoom (@TheShadeRoom) May 14, 2025
Additionally, the prosecutor read aloud a text Cassie sent to Diddy on one occasion. “I have all these sores on my tongue. I have another UTI,” it says.
By: Jadriena Solomon
#4
On The Stand: Cassie Talks Sex Club Experiences Alongside Diddy
On the stand, Cassie explained that Diddy also allegedly convinced her to go to sex clubs in Los Angeles. On one occasion, Diddy allegedly had sex with one of their male escort’s girlfriends.
Cassie testified Diddy sometimes convinced her to go to sex clubs in LA and Vegas. She recalled one escort bringing his girlfriend, and she had sex with him there.
When she expressed discomfort, saying, “I’m not into seeing the person you’re in love with somebody else,” Diddy…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Jadriena Solomon
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On The Stand: 2013 Alleged Assault From Diddy Resulted In Gash On Cassie’s Face
On the stand, Cassie shared that in 2013, while she prepared to attend Drake’s musical festival in Canada, Diddy became involved in an altercation with two of her friends. Amid the ordeal, she alleges, he threw her into a bed frame, which left her with a gash above her left eye.
Cassie testified that in 2013, while she was packing to go to Drake’s music festival in Canada, Diddy scuffled with her friends and threw her into a bed frame causing a “pretty significant gash” above her left eye.
After getting stitches, she texted him a photo saying, “So you…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
After the incident, Cassie says, one of Diddy’s bodyguards, D-Roc, to her to the doctor.
By: Jadriena Solomon
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On The Stand: Cassie Recalls Diddy Kicking Her Off His Boat
The singer also described an incident in Cannes, saying that Diddy kicked her off his boat under suspicion that she had stolen drugs. Her passport was still on board. She later attended a red carpet and movie and ultimately returned home on a commercial flight. She said that she “traded” her plane seat to get away from Diddy, but that he made the same move, and threatened her on the flight by showing her freak off videos. The singer testified that she felt trapped.
Afterward, the court took a break.
The court is taking a lunch break and is expected to return around 1:15 p.m. ET.
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
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Prosecutors Swap Freak Off Videos Of Cassie For Still Images
In her opening statement, prosecutor Emily Johnson vowed to show videos of Cassie pretending to enjoy herself during “freak offs.” However, on Wednesday, Johnson went a different route, displaying still images and having the singer explain them. Jurors had various reactions as the pictures were shown: wide eyes, head shakes, and intense focus were some reported.
Prosecutors showed five still images from videos recovered from electronic devices Cassie provided investigators.
One juror’s eyes widened as the first image — of Cassie and a male sex worker she identified as Jules — appeared on a screen in front of him. Another juror shook his…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
The images were only shown on monitors in the jury box and the witness stand, where Cassie was sitting. Prosecutors gave the judge and Diddy’s defense a binder with printed images. According to courtroom coverage from TSR, Diddy discreetly thumbed through the binder at one point before closing it and handing it back to his lawyer, Marc Agnifilo.
The images were shown only on monitors in the jury box and witness stand. The feed was cut to the public gallery and overflow rooms because of their sensitivity.
Prosecutors provided binders with printed copies to the judge and defense counsel.
At one point, Diddy asked his…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
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On The Stand: Cassie Details More Instances Of Diddy’s Alleged Violence
As her testimony continued, Casandra told the court of other instances where Diddy was allegedly physically abusive, a habit that began during the first year of their relationship, Cassie said. According to courtroom coverage:
“She recalled one incident in New York City where Diddy hit her in the head in an SUV, causing her to fall to the floor. Cassie also recounted a 2009 event in Los Angeles, where after speaking with a music producer, Combs called her a derogatory name, prompting her to slap him. She admitted she had been drinking and did not see any injuries afterward.”
Cassie also testified about an instance where she had to stay at the London Hotel for a week due to her bruised face. Diddy had allegedly assaulted her for 10 minutes straight by stomping her face in a car. Per TSR reporting, Cassie also said:
“An assistant, Genevieve, brought [Cassie] ice cream during that time. Ventura said she didn’t feel free to leave due to Combs’ threats, access to guns, and her fear of his power. She confirmed no one took her to the hotel out of concern after the assault.”
Cassie testified that during one incident, Diddy stomped on her face while she was on the floor of a car for about ten minutes. When she tried to escape, his security, Roger Bonds, forced her back and told her to go to a hotel.
She was then snuck into the London Hotel with her…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
Then, there was also a recollection about the singer hiding the “truth” from her mother, and being able to avoid seeing her due to a lack of FaceTime at the time.
By: Cassandra Santiago
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On The Stand: Cassie Describes Breaking Up With Kid Cudi Out Of Fear
On the stand, Cassie testified that one time Diddy beat her, leaving bruises on her face at a hotel after she left a party with executives from BET.
Additionally, the singer confirmed that she briefly dated rapper Kid Cudi (real name Scott Mescudi) in 2011. Sean Combs uncovered their relationship after going through her phone, and seeing an email about Cassie visiting Cudi. He allegedly reacted by threatening her with a wine opener while upset. Afterward, she called Cudi using a burner phone and fled to his house. After speaking to Diddy’s assistant, Capricorn Clark, Cassie returned to Combs’ location, and he again kicked her, leaving a bruise, and threatened her with freak off videos.
She later found her hotel room trashed with urine on the floor and feces in the toilet, and responded by emailing her mother and Diddy’s assistant, Capricorn, during a flight to the East Coast. The message allegedly revealed that Diddy had threatened to expose explicit videos of her on Christmas and threatened her and Kid Cudi’s safety while he was out of the country.
While visiting her mom in Connecticut, Cassie admitted that she lied about the abuse being the first time, and didn’t disclose the freak offs. However, her mom took pictures of her bruised back. Kid Cudi had also visited her in Connecticut for a few days, but Cassie said she broke up with him out of concerns for their safety. After that trip, she visited Diddy in Arizona, and he allegedly spoke of blowing up Cudi’s car. The two men later had a confrontation over the threats to Cudi’s vehicle, but Diddy denied any knowledge.
Cassie testified that during a meeting between her, Diddy, and Kid Cudi, Cudi confronted Combs about threats to his car, and Diddy denied knowledge, ending the discussion.
She also identified a photo of her and Diddy in Jamaica for SoundClash, confirming she was bruised at the…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
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On The Stand: Cassie Says At Least One Staff Member Was Aware Of Abuse
While testifying, Cassie periodically circled back to violent incidents with Diddy. She described an instance of him beating and kicking her as she tried to hide behind a toilet during an after-party. The violence only stopped when two men, D-Roc and James Cruz, entered the room. After that attack, Cassie says D-Roc texted her about needing to “ice” her face. Additionally, the singer said she witnessed Combs being violent to others, such as dragging an assistant out of bed, punching someone, and dragging another in Turks & Caicos.
Cassie testified that after one beating, D-Roc texted her saying, “Where you at? It’s time to ice your face,” showing awareness of the abuse and concern. She confirmed there were more instances of violence beyond what she had already described.
Ventura said she witnessed Combs…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
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On The Stand: Cassie Describes Two Instances Where Diddy Put Hands On Her Friends
Cassie described an instance where a friend had come to stay at her apartment on the 17th floor of the 875 Comstock. When Sean Combs got to the apartment, he allegedly “held” Cassie’s female friend and threw her on the patio furniture on the balcony.
On a different occasion, Diddy allegedly hit her friend of 17 years with a hammer in the head. Cassie has not spoken to that friend since the incident, saying that the moment “ended [their] friendship.”
On another occasion, Cassie said, she saw Diddy hit a different friend who she had been close to for 17 years in the head with a hammer.
“It just ended our friendship,” Cassie said. She hasn’t spoken to her since.
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
#12
On The Stand: Casandra Says Diddy Assaulted Her In 2018 When She Tried Ending Relationship
By 2018, after about a decade of dealings, Cassie testified that she attempted to end the relationship. Leading up to that, the singer said she began experiencing post-traumatic stress disorder that included blacking out and sleepwalking. “In my mind, my body told me I just needed to chill out,” she said on the witness stand.
Cassie testified she saw Combs on a subsequent occasion and had a consensual encounter with him. She explained: “We’d been together for over 10 years. You just don’t turn feelings off… like, I didn’t hate him.”
— TheShadeRoom (@TheShadeRoom) May 14, 2025
Also, at one point in 2018, Casandra said Combs forced his way into her Los Angeles apartment and sexually assaulted her after she tried to end things between them. They had initially met for dinner in Malibu, but he later came to her home and refused to leave.
Cassie testified that in 2018, Diddy Combs forced his way into her Los Angeles apartment and sexually assaulted her after she told him she was ending their relationship. She had met him for dinner in Malibu, seeking closure, but he later came to her home and refused to leave.
— TheShadeRoom (@TheShadeRoom) May 14, 2025
By: Cassandra Santiago
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Cassie Reveals She Wrote Tell-All Book & Settled With Diddy For $20M
During the last bit of her testimony for the prosecution, Cassie spoke on the bombshell lawsuit she filed against Diddy in November 2023. At the time, she sued him for assault, abuse, and sex trafficking. They settled within 24 hours, but kept the terms undisclosed. In Wednesday’s testimony, Casandra revealed that she had requested $30 million for the book she wrote with her mother about her experiences with him. Before then, she had attempted to walk into traffic from the emotional trauma, but her husband, Alex Fine, stopped her. The pain he caused, she said, was rooted in shame.
Ultimately, she and Diddy settled the lawsuit for $20 million, but at first, she said Combs didn’t take her seriously. Despite the private settlement, Cassie also explained why she decided to testify against him.
“I can’t carry this anymore. What’s wrong is wrong,” the singer said.
Court has adjourned for the day. Keep up with the overall Diddy trial updates HERE.
By: Cassandra Santiago